Purification of a methanol extract from the seed of Idiospermum australiense, guided by bioactivity on a rat brain cortical wedge preparation has afforded two known dimeric alkaloids, the piperidinoindoline (+)-calycanthine [1] and the pyrrolidinoindoline, (-)-chimonanthine [2] along with a new trimeric pyrrolidinoindoline alkaloid, (-)-idiospermuline [3]. Te structure of idiospermuline [3] was determined by spectroscopic methods and the absolute configuration by an X-ray crystallographic study of idiospermuline trimethiodide [4].
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[Research advances on chemical constituents from Calycanthaceae plants and their pharmacological activities].
Zhongguo Zhong Yao Za Zhi
May 2018
Lishui Institute of Agricultural and Sciences, Lishui 323000, China.
Calycanthaceae family comprises of four genera including Chimonanthus, Sinocalycanthus, Calycanthus, and Idiospermum. The plants of Calycanthaceae are popular ornamental shrubs and used as foods and medicines, which are mainly distributed in China, North America, and Australia. The plants of Calycanthaceae are rich in volatile components, alkaloids, sesquiterpenes and coumarins.
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April 2015
Chemical Biology Center, Lishui Institute of Agricultural Sciences, 827 Liyang Street, Lishui 323000, Zhejiang, China.
Plants of the Calycanthaceae family, which possesses four genera and about 15 species, are mainly distributed in China, North America and Australia. Chemical studies on the Calycanthaceae have led to the discovery of about 14 alkaloids of different skeletons, including dimeric piperidinoquinoline, dimeric pyrrolidinoindoline and/or trimeric pyrrolidinoindolines, which exhibit significant anti-convulsant, anti-fungal, anti-viral analgesic, anti-tumor, and anti-melanogenesis activities. As some of complex tryptamine-derived alkaloids exhibit promising biological activities, the syntheses of these alkaloids have also been a topic of interest in synthetic chemistry during the last decades.
View Article and Find Full Text PDFFirst total synthesis of trimeric indole alkaloid, psychotrimine.
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Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 263-8522, Japan.
The first total synthesis of (+/-)-psychotrimine, a novel trimeric indole alkaloid isolated from Psychotria rostrata, was achieved. In the total synthesis, the copper-mediated intramolecular and intermolecular aminations of halobenzenes, which respectively contributed to the construction of a pyrrolidinoindoline core and the installation of a third tryptamine unit, were used as key steps.
View Article and Find Full Text PDFSynthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids.
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Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano,via Venezian 21, 20133 Milan, Italy.
Hodgkinsine, a trimeric pyrrolidinoindoline type alkaloid, present as a major constituent of Psychotria spp. (Rubiaceae), has shown to produce dose-dependent, naloxone reversible, analgesic effect in thermal models of nociception and in the capsaicin-induced pain. SAR studies have been initiated by synthesizing the three diastereomeric dimers (chimonanthines) (11-13) which were evaluated in vitro and in vivo along with the synthetic intermediates.
View Article and Find Full Text PDFTo further understand the mechanism of analgesic activity and structural requirements of pyrrolidinoindoline alkaloids identified in Psychotria colorata, we here report the analgesic activity of the trimer hodgkinsine on thermal and chemical models of analgesia. Results show that hodgkinsine produces a dose-dependent naloxone reversible analgesic effect in thermal models of nociception, suggesting that activation of opioid receptors participates in hodgkinsine's mode of action. Hodgkinsine shows a potent dose-dependent analgesic activity against capsaicin-induced pain, indicating the participation of NMDA receptors in hodgkinsine-induced analgesia.
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